On The Yard

Annapolis is beautiful all year round, and each season brings its own unique flavor to this historic seaside town. If you’re visiting in the fall, you’ll be able to enjoy the special events that make it a popular autumn destination. From boat shows to fall festivals and everything in between, you won't run out of things to do in Annapolis once the weather turns crisp and the colors get brighter.

Can’t Miss Autumn Annapolis Events

Grab your calendar and get some of these locked in now. You’ll love the sheer variety of things to do when fall comes to Annapolis:

2023 Cultural Enrichment, Music, and Arts Festival, September 22 to September 24:

Check out the annual family-friendly CEMAFEST at the Westfield Annapolis Mall, where you can keep the vibes of summer going into the fall with a multicultural mix of live bands and DJs, food trucks, novelty arts and crafts, beer, wine and more. This fan favorite festival features cultural enrichment, live entertainment and music and art appreciation—and plenty of good times.

33rd Annual Kunta Kinte Heritage Festival, September 23:

At Susan Campbell Park at the end of City Dock in the Annapolis Harbor sits The Kunta Kinte - Alex Haley Memorial, marking where Kunta Kinte arrived in 1767 from The Gambia, West Africa. He was immortalized in Alex Haley’s Pulitzer Prize-winning Roots: The Saga of an American Family novel that became an Emmy award-winning miniseries. About one million visitors spend time here each year, and on Kunta Kinte Heritage Festival weekend, you can celebrate the perseverance, education and cultural heritage Kinte and his family’s journey represent at a free, family-oriented cultural celebration. Savor live music and dance performances, 100+ world foods and artisan vendors, education and community vendors, children’s activities and heritage and history of the African Diaspora. It’s an experience you’ll never forget.

Annapolis Baygrass Music Festival, September 30 and October 1:

Come to Sandy Point State Park to have a good time while you’re also helping the Chesapeake Bay. “Every Jam Saves the Bay” at the Annapolis Baygrass Music Festival, where you can experience a beautiful beachfront music festival featuring fourteen top touring bands, wonderful local food, microbrews, wines, craft cocktails/mocktails, workshops, craft vendors and fun for the entire family.

2023 Annapolis Powerboat Show, October 5 – 8:

For this long weekend, the place to be is the Annapolis City Dock, where one of the largest in-water U.S. motor boat trade fairs shows their boats. Have fun exploring “everything with a motor that floats on water” as well as a large lot of accessories and even courses, competitions, demonstrations and more. With the quaint backdrop of Annapolis and the Chesapeake a short ride away, the Annapolis Powerboat Show is a truly awesome boat-lovers’ weekend.

2023 Annapolis Sailboat Show, October 12 - 15:

A few days later, you can head back to the Annapolis City Dock for this annual crowd-pleaser, a perfect match for “The Sailing Capital of the U.S.” The international Annapolis Sailboat Show features a host of vendors with sailing essentials that range from high-tech navigational equipment to outboard motors. It’s another striking scene, with boats end-to-end in the Annapolis Harbor that you can explore and enjoy.

Art @ the Park, October 14 and 15:

Not far from the city center sits the bucolic respite of Quiet Waters Park, aptly named for its serene view of the South River, with 340 acres adorned with paved trails, boating spots, formal gardens, art galleries and a playground. Their two day art festival brings art vendors, musicians, food trucks, demonstrations and more for a perfect weekend out in nature. Take in the art everywhere around you.

Annapolis Jazz & Roots Festival, Starting November 4:

This highly anticipated annual event is a two weekend celebration of culture, history and jazz. Featuring live music and lectures, it honors the region’s deep roots in Jazz, Rhythm & Blues, dating back to 1926-1974 when Carr’s and Sparrow’s beaches held concerts, to the King of France Tavern and Maryland Inn’s ties to this art. Even world-renowned guitarist Charlie Byrd was instrumental to the popularity of this festival when he was artistic director at St. John’s College. Come and feel the rhythm move you.

A Fall To Remember

What are you waiting for? Plan a trip to Annapolis today, where the local seaside flavor is especially good in the fall. Don’t forget to take a USNA tour when you’re in town, so you can experience living history right on the Yard. You can book a hotel through NavalAcademyTourism to receive discounted rates; a portion of the proceeds from these bookings will directly support the Brigade of Midshipmen. The Naval Academy Business Services Division also helps the Brigade by donating proceeds from our 20 business units, enabling our midshipmen to be successful, well rounded future leaders. We support a number of extracurricular activities, such as cultural arts, theater, music, club sports and a variety of other activities. Happy fall, and hope to see you soon!

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